2 comments/ 8912 views/ 3 favorites Secretary - Day after Day By: AluminumDaisy Monday – Giraffe on Rollerskates There are a million "secretary" stories and fantasies out there. I have often used varying scenarios to help myself cum. Here is the beginning of one... (there will be more as I've completed Tuesday and Wednesday) She had just started the new job. A secretary. Well below her station, but the unemployment was running out, there were no jobs that fit her degree. She could copy, and email, so figured she was qualified. She wasn't sure exactly what her new boss did, but knew the pecking order was more of the traditional, meaning, she worked for him, and him alone. She sat outside his office, at a cute little desk. When she arrived, she was a bit nervous, but the promise of real money was motivating. She was getting a little bored sitting at home all day watching soap operas and game shows whilst treating her body like an amusement park in all parts of her apartment. The imagery was recycled to a point that she was grasping at the elements in her imagination to complete the task of orgasm. Of course, she knew once she got one, the second would come much easier and was worth the hours of rocking her ass back and forth over her fingers. The woman from HR gave her a quick tour. Copy room, lunch room, your desk, his office, parking pass, password to the computer. That was it. She realized, she still had not met her boss. Oh well. She sat down at her computer, logged in, perused the filing system. Now what? She sat and waited, the boss did not appear to be in yet. 20 minutes later her boss strolled through the office like he owned the place (and he could have, she didn't know). "You must be my new slave, ha ha, just kidding, I mean secretary", he winked. We shook hands as I stood. He looked a bit surprised. "Well aren't you kind of tall?" She was above average at 5'-10", but she didn't know any different and just lived a bit higher than everyone else. Also, because she was so tall, she could get away with not wearing high heels. She didn't feel the need to be over 6'-0" tall and be even more of an anomaly. She neither wanted to stick out or disappear. He said that he'd get her something to do shortly and to just hang tight. She sat back down and thought, it won't be too bad. At least he has a sense of humor. His eyes had a glint in them too, something she couldn't put her finger on. Almost like he knew something she didn't and found great amusement in it. 10 minutes passed and a voice came from a box on the desk. "Please come into my office, I found something for you to do." He told her that he didn't have much in the way of copying and typing right now, but he did have a requirement of high heels at work. He had an extra pair his previous secretary left, but they would be far too small for her. He pulled out a credit card and instructed her to buy one pair of black high heels. They could be any style, but had to be 3-4 inches high. She was to wear them out of the store. He instructed her to walk as slow as she needed and to bring the shoes she had on, back to him. This seemed a bit odd, that her boss would dictate what she wore, but she figured he just had some power trip thing going on. She needed that job, and if he was going to buy, why not? The sales lady thought it strange that she wanted to wear them out of the store, especially because she looked like a giraffe on roller skates, very inexperienced and unsure of herself. The walk to the car took ages and she regretted picking a store in the mall so far from the parking garage. She was also regretting driving a stick shift car, because the area to hit the clutch was so much smaller in the new shoes, her foot kept slipping off. Not a very smooth trip back to the office. She stood in front of her new boss with the shoe box containing her old shoes and waited for him to finish his phone call. After he hung up, she put the box on his desk, displaying the awkward movement the shoes forced her into. He told her that those would do and that she looked freakishly tall, but his rules must be followed at work. He said that he emailed some things that needed to be completed by the end of the day, mostly copying and collating. She would spend most of her day slowly walking back and forth between her computer and the copy room. She took the shoes off after getting in her car and drove barefoot home. She didn't even stop to get groceries because she didn't have another pair of shoes. He kept them in his office, which he locked at night. It was past 9 pm so she found some canned vegetables in the pantry, ate them from the can, put the tv on sleep mode, massaged her aching calves a bit and was probably asleep before her head hit the pillow. She did have some interesting dreams about rubber bands, paper clips and staplers, her new tools of the trade. Tuesday – Naked at work She woke up feeling refreshed after her long first day at her new job. Then it came back to her, she had to go to work. She had been so used to waking up at noon, starting her day with a bit of rubbing and an orgasm, resulting in a glow and smile that got her through the rest of the day. She looked at the clock to see if she had time to do the same this morning. If she hurried, took a shower, and rubbed one out while she waited for her hair to dry, and then ate breakfast in the car, she should have plenty of time. Excited she jumped out of bed, knowing she would be returning to it with a clean, naked body to defile. It took a little more time to reach her goal than it usually does. Every time she would get close, she would lock her legs and point her toes. The pain in her calves, from the shoes yesterday, was too distracting and the moment to cum left. Eventually she got the image of herself naked, wearing just the high heels, walking through her new office, breasts bouncing... ahhhh there it is..... As soon as she caught her breath, she immediately started massaging her calves, realizing that she'd be wearing those shoes all day again! No time for round two today so a quick blow dry of the hair, grabbed an apple, smeared some peanut butter on a piece of wheat bread and hit the door. She left the high heels in the car the night before, so she left the house with just flip flops on. They looked a little strange with her silk collared shirt and wool skirt, but were just to drive in. Once she pulled into the parking lot, she moved her seat back and put the high heels on. They did elongate her legs and make her push out her breasts, making her look more feminine. She had a thought back to the image that finally got her to cum. It brought a smile to her face, how ridiculous that would be, naked at the office... Her boss was in before her today. She set her things down, powered up the computer and stuck her head in the door to see if he needed anything. He said to check her email and re-read the instructions for the work he had her do yesterday. She read the email and found that she mis-read some of the instructions. Much of what she did yesterday would have to be redone. There was also an email from her boss written at 6 am, nearly 2 hours ago. It was marked "high importance". Uh-oh, she thought. My first day and I'm already getting in trouble! "Your lack of attention to detail has cost both of us our time. We can never get it back. When you were hired it was assumed that these tasks could be done by a 2 year old. Is that what you are, a fucking 2 year old? Stop acting like it. When I give direct instruction, it should be done just as I say and in a timely matter. Do not be a stupid cunt. I am aware you are new, and you do not understand how I work, but what happened yesterday is UNACCEPTABLE!!!! Punishment will be spared, but you will fix your mistakes on your own time. If this means you are here all night to fix your fuck up, fine. There will be no sympathy from me or any other staff. This is how I work. You don't want to end up like my previous secretary, do you? Straighten up, go give yourself a pep talk or something. Priority one, fix your fuck up. Priority two, come see me. Priority three, lunch break – it will be 3 minutes today. You have a lot to do today and I anticipate you will not be getting paid for it. -the boss" Her eyes were wide. She was breathing deeply and timidly. She was wet and slightly stimulated, like a hum, but was more concerned that she infuriated him so easily. It was her first day and now he thinks she is a "stupid cunt"? How could this be? She is smart and educated, sometimes funny. She did as she was told and went to the restroom, stared at her reflection, trying not to cry. Trying not to show a weakness, even if she was the only one there. "I want this job. I need this job. I will do whatever it takes to keep it. Even if boss is a little hot headed, I can handle this. Just do it." She fixed a bit of her mascara, opened the restroom door and walked out, head held high, chest out, but still with an awkward gait. She re-read all of the instructions to ensure she did it to the "T" this time. Her feet and legs were screaming at her to sit down, but she couldn't. She went through all of the same back and forth on the high heels as yesterday, but this time she was showing drive. It did not take as long, but it was 5 hours of constant work. 5 hours she would not be paid. She would not leave until at least 10 pm! As told, she stepped into bosses office. He did not ask her to sit, but started his thoughts on health and the body. She remained standing, shifting her weight to try and alleviate the twitching muscles in her legs. He told her he thought the body was a temple. It can provide so much. The value to feel both pleasure and pain is a gift that most ignore, focusing on the shallowness of solely "the good" while limiting "the bad". He felt that true pleasure could not be felt, unless it was equally balanced with pain. He revered health both in himself and those that surrounded him. He demands that all of his secretaries get exercise and follow a healthy diet that he dictates. This would start with priority 3, lunch. She was given three minutes to eat a sprout sandwich, an orange and drink 16 oz of milk. She could not finish and he explained that she must eat everything in his diet. He allowed her another 2 minutes to finish. Next he explained the exercise regime. She was to arrive 30 minutes early and stay 30 minutes late, on her own time, to use the treadmill in his office. He pointed into the corner where a machine was folded up against the wall. He pointed out that he had time yesterday to determine her size. He showed her the required exercise clothing. The t-shirt, it looked a bit small and she imagined it would hug her breast tightly. The shorts were short, but should not be a problem. The shoes were her size, but a wedge style, he said for safety. They were still 3 ½" high. She thought the shoes would be a challenge. He made a point that the exercise clothes he was allowing her to use were the only clothes allowed during exercise. She thought that was a strange statement, and then realized what she would not be wearing, her underwear and bra. That will feel weird she thought, especially because in the past, exercise made her vagina very wet. She had no idea why, but now there would be no barrier. Another realization, this means she won't be leaving until at least 10.30 pm!!!! He asked if she understood, then told her that he had more tasks to do in her inbox and to not fuck them up. She read through the tasks several times. Luckily, none of them required much walking, so she spent most of the next 8 hours typing and answering phone calls. Before the boss left, he gave her dinner in a container that could be microwaved. He instructed her that this was all she was to eat until he gave her breakfast the next morning. She agreed and went back to work. She finished up the typing around 9.45 and went into his office, which he now kept unlocked. She did not find a need to change in the restroom as she had been there alone for hours. She look off everything, including the shoes, she snickered to herself, "I guess being naked at work wasn't so far off". She put the exercise clothes on. Indeed the shirt was tight, but her breasts were still perky enough to look good without a bra. She finished dressing and started her 30 minute walk. It was not as bad as she thought. The desk work gave her legs a rest, so this was more of a focus of not looking like a giraffe. She made it home by 11 and resisted the urge to snack on anything. She collapsed on the bed, face down. She thought it'd be nice to have an orgasm, but she was so exhausted! She put her hand between her legs, just to check, it was very wet. She thought she may get a quick one in before she falls asleep. She started rocking back and forth, brought the second hand down for pressure and thought of work and that email her boss sent. She fell asleep in that position, fingers in the lips of her wet labia. Wednesday – Yelling Vagina She woke up sore. Her head was turned to the right, her arms were beneath her body. She didn't even take her shirt off. She was starving! Then she remembered that she was supposed to be to work 30 minutes early. She couldn't even fit in a pre-work orgasm. This is annoying she thought. All to keep a job? What will he know if I have a quick snack before I go? Then she thought better of it. He mentioned something in his email yesterday about what happened to his previous secretary. It must have been bad if she wasn't there. She showered and got ready. She noticed that the dull pain in her calves wasn't as bad, but her ass was throbbing. The 30 minutes of walking straight must have done something to those muscles. She put the high heels on in the car again and walked into work. Her boss was there early again. She went into his office and didn't make eye contact, just picked up the workout clothes that she had put down last night. She did notice they were folded differently than she typically does it, but didn't worry about that. She started to walk out to use the restroom to change, but he said he would prefer she use his private bathroom off to the side. He said it was more private. She didn't even know he had a private bathroom. It makes sense given how long he's in his office and doesn't come out. She quickly changed, hoping the quicker the 30 minutes were over, the faster she could have breakfast. Something she had not considered last night while she was walking, was that when the boss is here, he has the perfect vantage to watch her struggle with getting used to the shoe height. She was suddenly feeling vulnerable, but did not want to disappoint. The urge to hold her bouncing breasts and cover the hard nipples was strong. Thinking about her nipples got her focused on the wetness in her shorts. The friction between her labia was not helping either. It was a stream turning into a raging, warm mess. The boss said nothing, and appeared to be reviewing some printed forms. When she was done, she changed back to what she wore to work. He asked her to sit in one of the two chairs across his desk. He started talking about the tasks for the day. She was trying to listen, but the hunger in her belly was distracting. He asked her something about a stain, she snapped out of it. Sorry boss, can you say that again, I was a bit distracted. He gave her a stern look, like "how dare you"! He asked the question again, "I noticed that there was a dried white spot in the exercise shorts. This is a very personal question, do you pleasure yourself?". The question took her breath away. How did he know, she thought. She answered slowly but honestly. "Yes, I have for as long as I can remember. Before I got this job I would do it up to 4 times a day. There was nothing to do and it helps me clear my mind. I do a lot of thinking during the build up." He then asked if she found the walking "pleasurable". She did not say she liked it, but didn't say she didn't. She did explain that she had noticed in the past when working out that she would get wet. He then asked her if she remembered what he said about pleasure and pain being a balance. That to enjoy pleasure, it must be contrasted with pain. She did, but wondered where this was going. He asked if she felt her life was out of her control. Her quick response would have been no, that's silly. She is educated, well spoken, has a few very close, loyal friends. She can be the life of the party, or the wall flower. Before she could answer, he put up his hand in a "stop" motion, and told her to go to her desk and think about that. That would be her work for 1 hour. She was to make a list of the parts of her life. After that, she was to continue the tasks he had sent to her email. He would call her in when he was ready to hear her reasoning. As she sat down and wrote down the compartments of her life she had a thought that this is the perfect topic to work out while masturbating. She immediately had a response to that, plus the unfinished business the night before, plus the walk. She was still hungry, but her vagina was yelling louder for attention. Her list contained: Family Apartment Student Loans Car Sex – or orgasm They were in no particular order, but written out like this, her life seemed small. Uncomplicated. She really thought about the question. Control, vs out of control? She was not very close to her family, but they got along. She immediately got hung up. How could she control family? Her apartment was in constant disarray. She could imagine word getting out of its messiness, she feared animal services would take her cat away if they saw the condition. She also feared if she got in some kind of accident and a family member, or worse a stranger saw it, her secret of unkemptness would be revealed. Her apartment was out of control. Her student loans were automatically deducted, so they were in control, but not by her doing. If technology did not allow it, they would be out of control. Her car was like the apartment, so it was out of control too. Now for the one near and dear to her heart, orgasm. Of course she's in control, she has them all the time... but that's not the question. Do they control her, or does she control them? Hmm, her mind wandered to her wet pussy and how she could go get a little relief by going into the bathroom stall... a light turned on. She assumed her orgasms were controlled, but really they had been running rampantly out of control her whole life. How was it this was just revealing itself. After an hour, she put the list away and tackled the other tasks, her stomach growling. It was nearing lunch time when she got the call to go his office and bring the list. Her conclusion to him was that her life was generally out of control. They went through each aspect. He asked questions, trying to determine what his secretary needed. First, he asked if she wanted to be in control. She said she didn't know, her life has been like this forever. She wouldn't know what control was. He suggested an experiment to see if she could handle a little balance in her life. He proposed the next time she had the urge to pleasure herself, she should put a butt plug in for 10 minutes. He pulled out a green butt plug. It didn't seem like a such a hard thing she thought. If this will help her gain control of something in life, she was willing to try it. He did not see a terrified reaction, so the next question was if she had ever had anything in your anus? She had boyfriends get confused about where they were putting their penis, but she quickly redirected them to her warm pussy. He got a smirk and informed her they were trying to have anal sex with her. She did not know then what her reaction to the plug would be, and was slightly nervous. He told her to go wash it and put it somewhere she can access it anytime. He did add a caveat, that no matter what, when the plug was in, she was to resist the urge to pleasure herself. Secretary - Day after Day She agreed that this was a nice test. He had her complete the remaining work, 30 minute walk at the end of the day and she was home by 6 pm for the first time that week. He had fed her lunch, which she eagerly ate even though there was no time limit imposed. He had prepared an afternoon snack and dinner, which she took home. The whole night to herself, what to do? She puttered around, started laundry, did some old dishes, fed the cat, etc. It was then only 7 pm. With all this time, the thought turned to finishing what she started last night. She got up ready to lay on the bed and rub her way to an orgasm when she remembered the plug. Before the boss left he had handed her a bottle of lube. She had never used lube before as she was usually plenty wet by the time she would be ready for sex with her boyfriends. He said it was important to use it. She lubed the plug, pulled down her pajama pants that she wears at home, went down her underwear and attempted to insert... it was like a wall. She concentrated, but her vagina was yelling, she had to ignore it. The angle was awkward, maybe if she repositioned and slowly sat on it? She tried and with a few deep breaths, it was in and she wanted it out! She glanced up at the clock to start the 10 minutes. She sat with the plug up her ass, afraid to get up, trying to block the pain. Her upper body was swaying, trying to find a better position that did not make her feel like a shit the size of China was stuck. She took her mind off of things, making lists of other things she could do rather than pleasure herself because if she knew herself, as soon as the plug was removed, it would need to go back in. She was correct, the plug was in for a total of 50 minutes in 10 minute increments until she had decided to read a book and go to sleep, frustrated, horny and out of control. Thursday – Grain by grain What a restless night! She could not keep herself still! Her eyes were red, her pussy was dripping, her nipples were sensitive. She tried to remember the last time she had gone so long without an orgasm. She was feeling like an addict in withdrawals. She knew that if she touched herself once, it would be all over. Even wiping herself after pissing was uncharted territory and too much of a temptation. Rather than the jumping out of bed to rush back and complete the job of getting an orgasm, she slowly went through the morning routine, without orgasm. She was hungry again. Waiting to get to work for breakfast made her grouchy. She thought she would mention that to her boss. She didn't know how he would react to her suggestions, but this morning was not an inspired one. She did the same as days previous, putting the 4" high heels on in her car, so that when she saw her boss, she was abiding by his rules as his secretary. He was in the office again, before her. Maybe he enjoyed seeing the 30 minutes of free breasts, bouncing as she was slowly learning to walk in her exercise, 3.5" wedge heels. This morning, he did not try to hide that he was staring at her. He stared at her like he would a race horse during its morning workout. While she was a bit uncomfortable with him watching, she felt a twinge of pride. He thought that she was worth watching and that made her blush. As she completed her time and was folding the treadmill up and away, he stood from his desk and walked toward her. To this point, he had never touched his secretary. With swift, sure hands he reached between her legs, pulled away her short shorts. He felt the moist warmth that was created by his mandated exercise. She was so shocked she could not move. It all seemed benign up until this point. He did not linger, but rather immediately took his tainted fingers and headed to his private restroom. As he was washing, he ordered her to come to him. He told her that obviously she did not take his experiment seriously. If she had, she would have had the butt plug in during her walk. It was without doubt that walking in the high heels caused her pleasure and she was not able to control herself. She tried to explain herself, but he shooshed her, put his hands over her lips. She was frightened now and he saw it in her eyes. He slowly took his hand away. He dried his hands, and asked her to follow him and take a seat in front of his desk. He sat behind his desk. She was still in her exercise clothes and felt a bit weird, a little exposed. He explained that for there to be a change, she must listen to him. His only goal was a happy, healthy secretary. He then asked her to explain how the previous evening went and if she used the butt plug. She told him that each time she took it out, she had the urge to pleasure herself, and so she put it back in. He asked if using the butt plug made her more or less aroused. Her immediate thought was it took all arousal away! She hated that thing. But then she thought of the 3rd, 4th, and 5th times, the sensation of removing the plug. How there was a cold void. He could see the indecision in her face and suggested that perhaps she was unsure the affect the plug had on her. His next suggestion seemed outrageous. He had the idea to install a slightly larger butt plug to her chair. This way, anytime she was seated at her desk, she could think about the affect it has on her. It would just be for today, and it would be lubed every hour, but this way, she could determine if it was bad/good feeling, or a bad/bad feeling. He had a hunch he knew which one it was, but wanted her to discover it for herself. While she changed into the clothes she arrived to work in, he got to work modifying her chair. He stood back as he watched her pull up her skirt and try awkwardly to pull her panties aside while sitting. He made the suggestion that she remove them and put them in one side of her bra so they didn't get lost. That seemed reasonable to her, so she sheepishly removed her panties and stuck them into her left bra cup. This made sitting on the plug easier, but no less painful. She was shocked at the difference between the green one she used last night and this black one. There was no wiggling or adjusting. She was good and impaled. He instructed her to complete the tasks in her inbox. She read through everything and realized her tasks could only be accomplished by going back and forth many times to the copy room, much like her first and second days. Every time she got up, relief, every time she came back to her desk, the agony of reinserting the plug. She could not sit without inserting it. She also felt a bit aloof as her breasts appeared lopsided. One slightly bigger with odd lumps, and the other, normal. She did not know the self conscious affect on her was akin to humiliation. Finally it got to be too much, she hadn't had breakfast, she'd been impaled more than 8 times and she hadn't cum in days! She went into his office. He looked a bit surprised to see his freakishly tall secretary standing there when he had not requested her presence. She looked desperate, but she was afraid to say the first words, almost as if she was regretting even coming in. He said that she was there for a reason and to explain herself. She said one thing, "I'm hungry". He wondered how long it would take her to request food. He figured it would have been a few more days for her to gather the guts. He asked if the hunger was painful and if that was why she was there, requesting food. She nodded, not saying anything. He opened the side drawer of his desk and produced a bowl of cold rice. She was told to walk to the front of his desk, turn and face the office door, then get on all fours. She timidly did as she was told, carefully eyeing the mysterious bowl of food. He came around and placed the food on the floor in front of her. She stayed in that position, unsure if she could wait any longer to satiate herself. He walked back behind his desk. After he sat down he told his secretary she may eat, but, she may have one grain of rice at a time, her hands must hold her ankles and her skirt was to be lifted so he could monitor her ass hole and it's now larger size. This was a lesson in pain and pleasure. It would not be a quick lesson, but that was the intent. It took her 2 hours to painstakingly finish her bowl. Her legs were cramping, her feet had been asleep for who knows how long. One thing she did appreciate was not having the plug going in and out of her ass. Finally her belly was full. When she was done, he instructed her to return to her desk, and the chair with the plug, and complete her tasks. Also, that if she was ever hungry again, she was to kneel in front of his desk in that position, it was the only way he would know if she needed food. While she was happy to have quenched her hunger, she was not looking forward to sitting on that plug the rest of the day. After she was done for the day, she returned to his office for her 30 minutes on the treadmill. This time, laid out, were only shorts and the wedge shoes. No shirt. She was going to have to do it topless! She did not sign up for this! And then she had a flash of rent due next week, and had no idea where the money was coming from. She changed in the restroom and came out, tits bouncing, bouncing. She couldn't resist the urge to support them with her hands, so she cupped them together. Under his watchful eye, he only said "add one hour to tonight's walk and tomorrow morning's. Do not touch your tits. You're not wearing a shirt or a bra for a reason". As she walked and walked to nowhere, her mind was racing for the reason not to wear a shirt. After 45 minutes of her boss watching her labor in the heels, he shut down his computer and left. She was relieved, but knew that she was only half way done! When she was done, she put the panties that had been in her bra, on, to cover her vagina. When she got home, it was a bit later, 7 pm. She was tired from the extra walking. She cooked the ramen he left on her desk on his way out, thankful that she had food. She tried to stop her mind from wandering, but her habit of turning to masturbation for comfort was immediately replaced by a green butt plug. She wore it most of the night. If there was a good thing, she found the green one wasn't as bad as the black one attached to her chair at work. Another discovery, she thought it actually made her more aroused, even though when it was in, she could think of nothing else than getting it out. After putting the plug in and out all night, it was time for bed. She adjusted her alarm clock to be up an extra hour earlier. She was in such a frenzied state, if she did not have discomfort/pain to distract her, she may just masturbate in her sleep. She decided the intent of this exercise was to prevent her from pleasuring herself, be it conscious or unconscious. She slept with the plug in. Not far from that plug was a pair of glistening labia and a clitoris, begging, yelling and screaming for attention. Friday – working a double She slept better than she had the previous two nights, even with the butt plug firmly in her ass. Getting up an extra hour early was not appreciated though. Her first move was to remove the plug, use the toilet and take a shower. The water on her vagina was pleasant, but a frustrating reminder that she should not touch it. Even drying off she was afraid that any instigation on her part would end in a failure. The inability to control her own orgasm. She wore a blouse and a skirt, as typical, with a bra and underwear, even though she knew they were not allowed for her 1.5 hour walk this morning. It was Friday, so she was looking forward to the weekend off. No high heels, no butt plugs, just hanging out. She arrived at work, walked in with her 4" heels on. For the first day since Monday, her boss did not come in early, although, she was there an hour and a half early herself. She set her things down and went into his office. She picked up the shorts and 3.5" wedge heels and put them on. She didn't feel the need to use the restroom to change, as she was not allowed a shirt, so it didn't matter much to her. She started her walk. Her boss came in with 20 minutes left to go. Rather than turning on his computer, he rearranged one of his chairs to face her. He ate his whole wheat toast, yogurt and apple as he watched her breasts, bounce with each step. She was getting better, more graceful at walking in the shoes, but it didn't come without some practice. She still slipped up a bit, stumbled a little. When she had completed her 1.5 hour walk, there was a sheen to her skin. A thin layer of sweat, highlighting her features. As he did the day before, but this time she was topless, he shoved his fingers into her wet pussy, gauging the degree of wetness the walking had caused. Instead of immediately washing his hands... he shoved them into her mouth and said suck. After wiping his wet fingers on her breasts, he asked her to turn around and bend at the waist and hold her ankles. He was checking to see if the butt plug was inserted for her walk, since it was obvious that walking aroused her. The experiment was put in place to try and control her pleasing herself. A little green knob was sticking from her ass. A good secretary she was! He was pleased. He resisted the urge to slap her open cunt, or her round ass and ordered her to get dressed, but to remove the green plug, wash it and bring it to him. When she was all put together she came out to find her boss behind his desk, waiting. He asked her to sit and hand over the plug, giving her feet a rest after the long walk. She hesitated, a bit reluctant. She had a connection with the plug, animosity aside. He asked if she had any thoughts about her control over her orgasms. If she was learning anything about pain and its different forms. She attempted to articulate that her first impressions had been wrong. She had an immediate response to what she should feel, but when truly evaluated she found the opposite was true. While she was screaming in her head for the plug to be removed, she missed it when it was gone. The pleasure of its removal was not the thought she would get. There was a weight of the plug inserted that was desired. She could not say that about the black plug, but of course, it was bigger. With boss in full possession of the plug, he made an announcement. He felt the intended pain to block her pleasure response was not working. Time for a different approach. He had installed a dildo next to the black plug on her office work chair. He wanted her to complete the tasks in her inbox while sitting on both. For this to work, he requested she remove her panties and place them in his top drawer of his desk. She slipped them off and put them in his desk. She pulled her chair out to sit down and her jaw dropped. She had no idea how this was all supposed to fit while she got anything done! Her boss came out to watch as she made her first sit down. His arms were crossed, watching intently. She pulled up the back and front of her skirt, to guide the implements in. She had a brief moment of what the hell am I doing, but pushed it aside as she hovered, unsure of how to proceed. Grasping the dildo, she eased onto that first, then found the familiar black dildo, lubed, but still pushing her beyond her comfort... at this point, she was oddly eager to sit all the way down. She felt full. The sensation of being tacked down, but from the inside was exhilarating. Her face did not show this excitement. The boss could see she was having turmoil. Just as he knew the butt plug task was not the "experiment" he had described, the effect was rewarding. She attempted to find a better position, but there was no give. She had a grimace on her face. He made a mere "hmpf" sound and returned to his office, arms still folded. She tried to work on her tasks... and thankfully, they did not need a lot of up and down from her seat. There were 3 times she had to make copies or use the restroom. At 11.45 am she received an email from her boss. In official terms, she was invited to lunch to celebrate her first week as his secretary. She replied "Yes" and added the note: she was looking forward to learning more about her new boss. At 11.58 her boss emerged from his office, coat on his arm. He offered her hand to imply that she was to rise off of the impaled implements in her ass and cunt. She quickly hit Ctrl+Alt+Delete to lock the computer and took his hand, picking up her purse and coat quickly feeling the cool void of both orifices. She wanted to turn and see if she left any wetness on her seat, but he was pulling her forward towards the door. He had a perfect view as she stood up and to his pleasure, the evidence was there, the pleasure of the butt plug was amplified by the dildo. This was going to be a fun weekend! They went to a quaint café. He ordered for both of them and she was acutely aware that she had no underwear on. She noticed when they got out of the car at the café that he had a gift bag, not large, something you would put a scarf or pair of gloves in. After he had ordered for both of them, she was presented with it. A "welcome to the club" sort of thing, he explained. Rather than open it at the table, she was told to use the restroom and put it on. She was warned the lock on the door was a bit tricky and to lock it all the way. She was intrigued and a bit perturbed, the blt and iced tea was not her "cup of tea". But it was part of her boss's requirements. As she closed the door she saw what he said about the lock and she double, triple checked it. She set the bag on the counter. She removed a pair of underwear, but it had attachments. It looked similar to her desk at work. There was plug – smaller than the black one and a dildo – smaller than the one at work. She walked out of the restroom, in her heels, breasts pushed out and two holes filled. She sat down with a smirk. He asked what that look was for, and she had no words. To fill the time she told him her mundane family story and he was cryptic. He wanted to know about her social life, living situation, etc. They finished eating and he took her back to work. When they arrived he asked her into his office. Once across the threshold, he asked for his gift back. She was sad. She thought this would be a more permanent thing. She was told that while at work, she was to be pantie-less and would sit at her chair as it was currently configured. After her walk in the evening, she was to put the gifted panties on and wear them until she returned for her morning walk. He also informed her that there was training she would need to better serve him. He hoped she was not busy the next day, Saturday, at noon. She confirmed that she did not have plans that could not be rescheduled. He said good and sent her home early, along with the panties. She was instructed to decide on her own healthy dinner and breakfast with what was left in her refrigerator and pantry, then clean them out bare, and unplug the refrigerator. She was relieved there would be no additional walking, as her tummy was full and feet tired. She was asleep by 3pm. Comfort in the fact she was full, front and back. Saturday – 93 degrees What a brilliant 15 hours! She needed that and was thankful to her boss for letting her leave early from work and sleep in. She was a little upset that she had to change her plans and cancel the brunch and shopping with her best friend because he requested her to be at training at noon on a Saturday, but was thinking this job was turning out okay. It was a bit eccentric, butt plugs, high heels, dietary and exercise requirements. If anything, it was definitely better for her than what she was doing on her own. She was becoming a better person because of her boss's control. This made her feel more confident that what ever was involved in training, was for her own benefit. She made her own healthy dinner the night before and was looking forward to a "clean out the fridge" omelet. The panties she received as a gift yesterday were only removed when she had to use the restroom. Getting the dildo and butt plug in and out was becoming easier, even in the 20 hours since she received it. There were a few moments of being uncomfortable, like when she bent over to pick up the dirty laundry, or when she was shaving her legs around the ankle. The angles were adding additional pressure. Secretary - Day after Day After she had cleaned up her last meal from her kitchen, she set to purging everything left over. He wanted her to clean all food out of her apartment to the point that she unplugged the fridge. After several garbage bags and a box to be donated to the homeless, all that was left was an open box of baking soda and cat food. She even got rid of her prized salt and pepper grinders. A little difficult, but she was focused on her future. She felt a bit weird, parking in an empty lot. No one working on a Saturday. She was unsure what to wear, something casual? She chose what she typically would, a smart blouse and A-line skirt. The shoes, she put on in the parking lot. As she walked in she didn't know if training required the 30 minutes of walking. She was arriving 30 minutes late already! The panic and flushness to her face were obvious. She set her things down and paused, standing between the desk and her bosses door, debating whether to broach the topic, or if she should just sit and wait for his direction. She bit her lip and went in. He was behind his desk and did not look pleased. She put her head down and approached the treadmill. Where her exercise clothes normally were, all she saw was a pair of 5" black patent leather high heels and a collar with a small leash. She was confused. She looked back to her boss sitting behind his desk, watching every move. She stripped, a pile of her stylish clothes on the floor. She put the shoes on and thought they were impossible. The extra inch made her feel like she'd never worn high heels. The collar was a bit awkward, she couldn't see the clasps, but felt her way around. She "mounted" the treadmill, feeling more animalistic with the lead dangling between her breasts. Today there was a note and an arrow, showing where to attach the other end of the lead. There was also a pre-programmed time and regiment. As soon as she attached the lead, the belt took off, forcing her to grab the side bars to keep up. She found that if the lead was kept at a certain tension, the speed was manageable in the ultra high shoes. The pull on the collar was all she could focus on. If she let it slack, her feet in the incredibly high shoes could not keep up. Her eyes kept darting down to the display in disbelief. 3.5 hours remaining?! She was completely naked and constantly concerned with her pace so as not to trip and hang herself by the neck. Her boss did very little sitting behind his desk. Mostly looking at his secretary struggle. She was determined, and bright to figure out the tension in the collar and leash influenced the treadmill speed. In another 10 minutes she would see the program he had installed. Random inclines would challenge her. Negative made the high heels seem higher, positive (uphill) gave her calves a rest. If she was to be walking that long, he had to give her some release, and challenge. About midway through, her boss stood up and approached a box on the wall. She had not noticed it before, but could only guess. He pressed a couple buttons and then left the room, turning the lights out. She was not in complete darkness, but it was different sensation. To that point he hadn't said a word, but she was trying to process the changes he had made since yesterday. She hoped that this was not punishment for her misunderstanding of the 30 minutes of walk before work. She kept her concentration on the tension in the lead, and not tripping. Being totally naked was the least of her concerns. She didn't know if it was her imagination, but it started getting hot. Not warm, hot. Her sweat was now dripping from her. He must have turned off the air conditioner and turned on the heat. It was like a sweat box! And with an hour to go! After the time wore down, the treadmill stopped on it's own. She was desperate for water. She removed the lead and rushed to the private bathroom, scooping handful by handful of water into her mouth. She even went to the effort of pooring water over her face and body. She did not think she could finish, but she had! After toweling off the sweat and water, she returned to her pile of clothes and put them on. She was unsure about changing the thermostat, but being a bit "green" went to the wall and turned it down from the 93 degrees it said it was at. She checked around the room, and then left to pick up her things she left at her desk. There was a note taped to her computer monitor, "That was punishment, not training. You are behind! Be here tomorrow at noon. Do not disappoint." She had a sense of extreme sadness overcome her. She failed her boss over something silly. She should have thought things through! She made her way to her car, the butt plug and dildo being a constant thought with the changing of her weight. She unlocked her door and saw a note on the windshield. It said, "You need food. Anything left in your pantry should do." She thought back, that means she's eating with her cat tonight. Great! She went home and watched infomercials. The cat food wasn't as bad as she thought, but her cat looked a little pissed. She was completely drained mentally and physically, apprehensive for tomorrow. A good thing, the instruments in her ass and cunt protected her from touching herself. That is all she wanted to do. Sunday – saying hello for the first time She woke up irritated and starving. He didn't know if her punishment would extend to breakfast, but she couldn't eat all of the cat food. The dildo and butt plug were getting more annoying than anything. Every where she went, they were there, rubbing her from the inside, constantly in her head. She was finding reasons to use the toilet, just to have a break. She had tried to stay at least mentally busy since her punishment yesterday, but the cat food put her in a bad mood and the tv was not rewarding. This morning she was going to go through her closet and find clothes to give away. She needed to drop off the food that she had boxed from her pantry, may as well take some clothes for charity too. She had forgotten that the food was still in her apartment! It was gone from the shelves and gone from her mind. Oooohh, her stomach growled. There wasn't anything particularly good sounding, from 5lbs of flour to soup that she never should have bought, but it wasn't meant for a feline, it was meant for a person. Her head was fixated on the food. Idle hands and the devil popped into her head. She got up and went to her bedroom. She turned up the radio and got to work. She would not fail. Her quest for control was not easy, but she was determined. By 10 am her closet looked neat and organized. The dresser drawers could close now, and all the old socks with holes were relegated to the linen closet as dust clothes. She loved finding new uses for things. Next to her socks, her underwear. She couldn't help think that she may never get to wear them, as they could not hold the implements that were violating her 24/7. The garbage bag with the ugly, or ill-fitting clothes was going right to the trunk of her car, and then the box of food. She needed it farther away, out of the apartment. She took a shower, removed the panties and carefully cleaned the parts, then reinserted, first the dildo, and then the plug. The novelty was wearing off and she found the lubrication that had been there before, was not. She was not enjoying the constant stimulation. On top of the hunger, the irritation grew. She managed to leave the house a bit early and arrived 40 minutes early. Plenty of time to get her 30 minutes in. She did as she had done before and changed her shoes from the flip flops she drove in to the 4" heels. Her mind went to the 5" heels she wore on the treadmill yesterday, oh they were hard to walk in! She went in to the quiet, dark office and put her things down at her desk. She went into his office to find it as she left it. She went to take her clothes off and put the collar and chain around her neck, next she changed shoes. She got on the treadmill, ready to attach the leash, just before she locked it on, she noticed the time, it wasn't saying 30 minutes, but an hour. That is unusual. She tried to change the time but it wouldn't let her. She attached the leash and figured she would just keep going until her boss came or the treadmill stopped. It took a few minutes for her to get back into the tension of the leash that controls the pace. She had started to "zone" out, putting the pain of her feet out of her mind when her boss came in. He didn't even look in her direction. She figured it was fallout from her disappointing him. She had 20 minutes left of the hour but since he seemed to be a bit grouchy, she decided not to bring up the time change. She hadn't heard his voice since Friday when he told her to go home early and wear her gift of panties. After he found a few things in his desk drawer he went into the bathroom and turned the shower on, letting it warm up. He then returned to the office and turned the treadmill off with a special key. He explained, that was the only way to override the program. He unhooked the leash from the machine and led her off the equipment. While she waited, bare chest out, he took his hand between her legs to gauge her wetness from her walk. Where she would normally be very aroused, he found, not a dry pussy, but not nearly as wet as earlier in the week. Rather than having her lick his fingers, he tasted her for the first time. He pulled her along, passed her pile of clothes and in to the bathroom. It was starting to get a little steamy and she was very curious if this was training, or more punishment. He lead her to the standup shower. It was larger than average with masculine slate colored tile and glass doors. He told her that this is her training and that she was a day behind because of her stupid behavior. He said her actions yesterday indicate that she is not learning. While her body is responding to the pain and balancing the pleasure, as indicated by his post exercise tests, her mind has not made the connection. The next step should help her internalize the need for mental pain, to achieve mental pleasure. He told her to get on all four inside the shower, ass facing the temperature controls. He got a towel and put it under her knees, that was not the pain he intended for her, he explained. The shower had been filling a jug with warm water. He tested the temperature, it was still too hot, so went to the vanity and retrieved a few tools. He brought what looked like tubing, lubricant and a butt plug that looked eerily similar to the one that had been installed to her chair a few days ago. She could not see what he was doing behind her, but she had a sense that this was not going to be fun. He admired her ass, and then quickly gave it a slap. A red impression slowly appeared. When his hand print was clearly visible, he slapped the other cheek slightly harder. She made a whimper sound at this, her tits swaying from the impact to her whole body. Her first thought was that was uncalled for, but then she put that thought aside, as what was done was done. It took her mind off the black butt plug within range of her ass. She heard the bottle of lubrication open and then close. He knelt down beside her, rubbed where his hand print was hot on her ass, then with precision, he guided something into her ass, and far. It wasn't as big as the other plug in her panties, so it wasn't entirely unpleasant. He made a few adjustments, and then she felt it. Like there was a heater, but from the inside. The coldness of the shower on her skin was being warmed from within, and then she felt the pressure growing. She hadn't eaten much food recently, but the feeling of full was growing. It was slow at first, but then it was uncomfortable. She shifted her weight from knee to knee. He gently started to massage her abdomen... a little coaxing. He told her she was doing great and they were almost half way there. He didn't see it, but her eyes got huge. She didn't know exactly what was going on but knew this was torture! When he had completed filling her up, he told her to close her anus as tight as she could, like she was holding back a fart. She put all of her effort into that. He removed the tube and then slowly coaxed the black plug in, sealing the liquid into her. She was shocked at how big the plug felt. Her muscles were starting to twitch and all she wanted was to push and push hard. He put a few of the tools on a shelf and began massaging her ass, being gentle around the burning hand marks. He then asked to sit up on her knees, hands on thighs. He stood up and put the zipper of his pants in front of her nose. He explained she was to control the water in her bowels at all cost. He needed pleasure and she needed pain. She was to suck his dick until he was sufficiently pleased. She had done this with a few boyfriend before, but not under so much pressure. She unzipped his pants, being careful not to get his underwear caught in the teeth of the zipper. She fished around inside his pants and final brought out his already hard dick. It sprung out at her, as if to say hello for the first time. She started salivating, wanting to start out being very pleasing to him. She started slow and unsure. Trying to get a glimpse of his face or any indication she was doing okay. She brought her hands up to help guide the rhythm. He said no, and she put her hands back down. He grabbed her leash and back of her head and started guiding to his liking. Her mouth was getting sore, but she kept thinking of being as wet and warm in her mouth as possible. The movement of her body to maintain his pace was making her insides very unhappy. Her stomach was cramping and she could not control anything. She tasted a bit of the pre-cum and knew it would be soon. She had to hang on a little longer. She thought she could feel the plug moving out slightly, if it got to a certain point, it would explode out of her. She started using her tongue, little flicks usually worked, and it did. He held her head hard against his scrotum, he was in as far as her face would allow. She had a hard time breathing, but stayed there, tasting the cum slide down her throat. It's funny, she thought how everyone tastes different. She started to hum, trying to get air. He let her head go and she gasped, trying not to spill an cum. She hadn't eaten all day, and this was her lunch. He reached over and turned the shower on. It was bit cold at first, but soon was warm. He started washing himself, ignoring her at his feet. When he was done, he had her get on all fours again. He leaned over and told her he was removing it, but she had to hold it in for 5 seconds before letting it all out. She nodded in agreement. She clenched as much as she could. 1 mississippi, 2 mississippi, 3 mississippi, 4 oh I'm going to lose it... 5 mississippi. She did it, and the pressure started to be released. She was feeling weak and ended up laying on her stomach, letting the warm shower hit her and the warm water leave her. It felt like days while she was lying there on the wet cool tile. When she final opened her eyes and thought the enema was over, she was surprised to find her boss gone. She slowly got up, very sore. She had the urge to sit on the toilet and found she wasn't quite done. She dried off and found a note next to a box of cereal and gallon of milk on her pile of clothes in the office. It said "See you at work tomorrow. You can only eat the food I give you, apologize to your cat. Don't forget the panties". Monday – anniversary She woke at her alarm. She wanted to hit snooze and rub on herself like in her previous life of unemployment, but was acutely aware of the screaming in her ass. She had never had an enema before, but found it stressed her muscles more than standing in the 5" heels. She was a bit more up beat at having dinner and breakfast with people food, even though it was just cereal and milk. Her experience with cat food was not pleasant and she was eager to distance it from her mind. She arrived on Monday like usual. Walked in with her 4" black heels on (their one week anniversary as it was). She set her things down and entered the office, ready for the 30 minute walk. She stripped in the office, not even changing in the bathroom because he saw all of her yesterday. He peeked up from his desk to watch her get ready, but did not say or do anything. To her surprise the shirt, shorts and 5" shoes where laid out. A walk without being nude sounded good. And the relief of not having to control her pace with the collar. Perhaps a reward, or punishment? She had a hard time telling. As she walked, her mind started thinking back to her training. He had said that her body was reacting, was being controlled, but not her mind. It was still only focused on pleasure, and was not balancing with pain. She wondered how in the world the mind could be in pain. How could her ass full of water train her to have pain in her head? Her immediate thought of the enema yesterday was the intense torture right before the release, when she had to hold it on her own for 5 seconds, and then the immediate relief, that continued as she drained. A flash came across her as she glanced down at the time remaining, 15 minutes. It brought a smile to her face. She made her boss cum. She wasn't sure he was ecstatic, but a man cuming in her mouth has always been well received. She realized that when she was sucking and licking him, the pain in her ass was there, but dulled. Her focus on him cuming, giving him pleasure over shadowed the intense cramping and ache in her belly. She thought there was something there, but her walk was up and she had to get to work. She felt the excitement of undressing twice in front her boss. He didn't do his check like he did in the past, where he gaged her arousal by testing the wetness of her labia. He would have found her a bit wetter today, as she was able to think about her bosses cum in her throat. As instructed on Friday, she was not to wear the gifted panties with dildo and butt plug, but was to be pantiless after the morning walk. She assumed that he would keep the large dildo and butt plug attached to her chair, but she was surprised when she pulled it out and there was just a regular chair. No instruments to torment her. She felt sad, empty, literally. She quickly sat down and powered up the computer and opened her emails. Her boss was in the habit of directing her via email with lists and lists of tasks to complete for the day. She sifted through the ones with the closest deadlines and started going. A window popped up "How is my secretary today?". She didn't think IM chatting was allowed, but then remembered reading somewhere on the intranet that they have an office communicator that is meant as a collaboration tool, for business use only. Oh course it usually was only used for inter-office romance. She hesitated and just said fine. Rather than using the intercom he used on her first day, her boss found the IM more private, and so called her into his office. Standing up was not as laborious as it had been before, and she sprung up to her 6'-2". She took her notepad and pen and headed in. On his desk was a timer, the kind they use for chess, that keep track of both sides of the game. He stood up and handed it to her. He instructed her to keep track of the time she either thought or spent typing in the office communicator (IM). He was going to ask her questions throughout the day. She was to reply in the timeliest way, but it must be truthful and accurate. When she was busy with her official tasks, the left clock would keep time, when she was thinking and typing about his questions, she was to be keeping time on the right clock. She was to work on the left clock, meaning, she needed 8 hours on the left clock before leaving tonight. There was no limit to the time on the right.